Thursday, January 31, 2008

POTW: Serial-preneurs

I have never worked for or in a big company, and have no desire to do so. Building great – hopefully, some day, big – companies makes me tick. In a perhaps sick way, I enjoy the uncertainty of creating and building versus the certainty of a paycheck. Prior to Crescendo’s growth – and my evolution from a founder into paycheck-procuring employee – I had gone 16 years without a job. I recall fondly the chuckle of my CFO at Crescendo when I asked (upon receiving my first paycheck): What’s all this FIFA and SDI crap they’re taking out of my pay? Big companyitis … could be the Peter Pan in me.

The emotional tonic of starting and building something is addicting. Once you’ve done it, it’s hard to get off the sauce; when you stray, it’s a lonely and frightening place. It reminds me of one of the Sacramento Entrepreneurship Academy's founding tenets: Entrepreneurs replicate themselves (and what they do). Security is morbidly scary.

I just unearthed a summer of 2007 article in the Journal, The Secrets of Serial Success: How some entrepreneurs manage to score big again and again and... It’s a navel-gazing story, loaded with meaningful morsels. A random taste:

More than anything, however, the greatest, and more crucial, challenge among repeat entrepreneurs is figuring out how to rekindle for future ventures the innocence, love and hunger that fueled their first enterprise...

So why do some entrepreneurs who strike gold once continue to start over? A general contractor might launch a business because he has certain skills, and then stick with it until retirement. Or a banker will work her way up the corporate ladder, happy with the security of a paycheck and benefits, and retire once she has saved enough. By contrast, serial entrepreneurs' main job is the act of creation -- and thus they keep creating new businesses, often after they no longer need the paycheck...

One of the hardest tasks serial entrepreneurs face is recapturing the drive and direction that fueled their first venture, without letting the first success overshadow or dictate what they do next. Sometimes, it's as simple as learning to let go...

Mr. Bricklin, who now runs Software Garden Inc. in Newton Highlands, Mass., says he feeds on the thrill of starting something new and untested. "It's like that sense of walking across a stream on the rocks -- sort of knowing where you're going, but sort of not." As for risk? "If you actually seen the ups and downs of a business, and your family isn't terrified, that makes it a lot easier to do yourself."
Having slipped on many rocks and stumbled through numerous streams, I love the metaphor. Particularly if you're doing so on your own dime and own time, venturing to a place uncertain.

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